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Holiday Rentals with Pools in George Town

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    Travellers to George Town are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in George TownView all 25 rentals
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    10 feet from the beach, Grandview has a grand view1 / 32
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Oceanview/Poolside Condo on Seven Mile Beach1 / 15
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fixed week rental, 7 nights, Saturdays changeover only. Also known as Holiday Inn Resort Grand Cayman. Free shuttle to Seven Mile Beach, 5 min. One Bedroom Suite One king bed One bathroom Living room with sleeper sofa Dining room and full kitchen Iron, ironing board,...
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    George Town, Grand Cayman KYI 1206
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Children's Pool
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fixed week rental, 7 nights, Saturdays changeover only. Also known as Holiday Inn Resort Grand Cayman. Free shuttle to Seven Mile Beach, 5 min. Two Bedrooms Suite Two king beds Two bathrooms Living room with sleeper sofa Dining room and full kitchen Iron, ironing board,...
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    George Town, Grand Cayman KYI 1206
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sprat Bay Luxury Villa1 / 24
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2017
    I checked in 25th of October and stayed at Sprat Bay for five days. We were a very big crowd, so 5 couples and 10 kids to be exact! I know right, quite a bit... and if we were...
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    About this property
    Ocean Front Villa with its own private beach and swimming pool located in South Sound. The villa is constructed on a 20,000 sq ft land in a tropical setting with tall palm trees. The living area is 6,000 sq ft has 3 living rooms, 6 bedrooms and 6 en-suite bathrooms sleeps up to 22 people. The villa...
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    George Town, Grand Cayman KY1
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 22
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Private Garden
    • Air Conditioning
    • Children's Pool
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fixed week rental, 7 nights, Saturdays changeover only. Also known as Holiday Inn Resort Grand Cayman. Free shuttle to Seven Mile Beach, 5 min. One Bedroom Suite One king bed One bathroom Living room with sleeper sofa Dining room and full kitchen Iron, ironing board,...
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    George Town, Grand Cayman KYI 1206
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the newly renovated ground floor, 2 bedroom unit at George Town Villas! Inside you will find big, sea-view windows where you see the beauty of the Caribbean waters. The open concept kitchen, dining and living area makes for the perfect place to gather after a sun filled day. The open...
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    George Town, Grand Cayman KY1 1002
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Ocean Views
    • Children's Pool
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully updated to a high standard in September 2017 condo unit #411. This ground floor 2 bed 2 bath condo has views of the delightfully manicured gardens, pools and the world famous seven mile beach. 1 minute walk and you're on the glorious white sand looking at crystal clear water. 2...
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    George Town, Grand Cayman KY
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury 6BR Oceanfront Estate with 150' Pool and 2 Hot Tubs - 'Point of View'1 / 45
    (8)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2017
    Close to central George Town, this villa was situated int he best location. The rooms were amazingly spacious and really comfortable. Everything was state of the art. I loved...
    Reviewed 29 January 2017
    Last year we rented "Present Moments", this year "Point of View" . The home was above and beyond expectation. It was beautifully appointed, fully automated...
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    About this property
    Introducing Point of View, a magazine-worthy South Sound villa that helps you focus on what's important: untouched natural beauty, simple luxuries, and distraction-free moments with family. The gentle waters and soft sands of the private, kid-friendly beach are perfect for even the littlest bare...
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    Location Information
    George Town, Grand Cayman KY1 1302
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Grand Caymanian Resort: Studio, Sleeps 3, Kitchenette1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Children's Pool
    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grand Caymanian Resort: Studio, Sleeps 3, Kitchenette. Fixed week rental, 7 nights, Saturdays changeover only. Also known as Holiday Inn Resort Grand Cayman. Free shuttle to Seven Mile Beach, 5 min. Studio One king bed and sleeper sofa (twin) Bathroom with whirlpool tub Microwave, coffee maker...
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    George Town, Grand Cayman KYI 1206
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Caribbean Paradise 91 / 12
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2017
    The condo was beautiful and the manager was very easy to work with. The beach is not like Seven Mile Beach. It is a little rocky but it gorgeous. It is very close to everything.
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    About this property
    This standalone 3-bedroom beachfront villa—part of a resort/condo complex—is found in a residential area where many Caymanians make their home (or second home). The lovely neighbourhood of Caribbean Paradise, in South Sound, boasts a sense of community and a beach with impossibly soft white...
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    Location Information
    George Town, Grand Cayman KY1 1202
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The condo has 3 bedrooms and 2 full baths. The owners suite has a comfortable King bed, the second room as a comfortable queen bed and the third bedroom has a Murphy queen bed that is also very comfortable. The condo is on the second floor and you can see the beach from every room, and it is...
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    George Town, Grand Cayman
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7BR “Tatenda,” a Luxury Cayman Villas Signature Property1 / 43
    (7)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Tatenda Villa is the best and well maintained property we have ever stayed at. The Villa feels brand new, luxury at it's finest. Ann, the Property Manager did a wonderful job at...
    Reviewed 3 weeks ago
    My week at Tatenda far exceeded my expectations! My room with my private bath had the most comfortable bed and bedding! (I'm picky) The pool with the salt water was amazing...
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    About this property
    Luxury Cayman Villas proudly presents “Tatenda,” a colonial estate located in the prestigious community of South Sound on Cayman’s Southern Shores. Offering the most exclusive collection of private, family-friendly, oceanfront villas in Grand Cayman, we carefully outfit each residence with our...
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    Location Information
    George Town, Grand Cayman KY1 1111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    Caribbean Paradise #121 / 22
    (8)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find paradise at this 3-bedroom, beachfront villa with a spacious back deck shaded by palm trees and looking out over the Caribbean Sea. Enjoy a memorable oceanfront barbeque with burgers on your private gas grill, and then kick off your flip-flops for a sunset stroll along the shore. This stretch...
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    Location Information
    George Town, Grand Cayman KY1 1202
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to coral bay village, your beachfront paradise. Located right on a secluded beautiful white sand beach, close enough to georgetown and the airport for your convenience, but far enough to enjoy the quiet and beauty without the crowds and rowdiness of seven mile beach. For less than the price...
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    Location Information
    George Town, Grand Cayman KY
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    'Nirvana' - A Luxury Cayman Villas Property1 / 38
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2017
    WOW! That's the first thing that comes to mind when driving through the gate to Nirvana. Private, spotless, breathtaking, just a few words to describe this villa. Kayaks and...
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    About this property
    Luxury Cayman Villas proudly presents 'Nirvana,', a one-of-a-kind, eco-chic oceanfront estate affording complete privacy, sweeping ocean views, private pool and wide, sandy beach. Offering the most exclusive collection of private, family-friendly, oceanfront villas in Grand Cayman, we carefully...
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    Location Information
    George Town, Grand Cayman 11302
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable, well-appointed 3 bedroom (and den) villa on the south coast of Grand Cayman is the perfect combination of peace and serenity in a very convenient location. It’s only a 5 minute drive from the airport and 10 minutes from the main town, George Town, and situated in one of the most...
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    Location Information
    George Town, Grand Cayman KY1 1110
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fixed week rental, 7 nights, Saturdays changeover only. Also known as Holiday Inn Resort Grand Cayman. Free shuttle to Seven Mile Beach, 5 min. One Bedroom Suite One king bed One bathroom Living room with sleeper sofa Dining room and full kitchen Iron, ironing board,...
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    Location Information
    George Town, Grand Cayman KYI 1206
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Ocean Views
    • Air Conditioning
    • Washer
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completed in 2012, this house is As Good As It Gets. Decorated from top to bottom by noted interior designers, the house was featured on the cover of Real Life Magazine last year and is one of the Showcase Properties on their website. This 5 bedroom, 5 bathroom beachfront home has it all: Living...
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    Location Information
    George Town, Grand Cayman KY1 1109
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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